Hydrochloric Acid → HCID 59625504, compound

HRID 2192821Notes

Reaction equation

HRID 2192821 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[C:16]([NH:25][CH2:26][C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:19][CH:20]=2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:3]1.C(N(CC)CC)C.[C:46](OC(=O)C)(=[O:48])[CH3:47].Cl>ClCCCl>[C:46]([NH:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[C:16]([NH:25][CH2:26][C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:17][C:18]([C:21]([CH3:24])([CH3:22])[CH3:23])=[N:19][CH:20]=2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:3]1)(=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59625311HCID 59625311, compound

Product 1

HCID 59625504HCID 59625504, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl (3R,5S)-3-amino-5-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (70 mg) in 1,2-dichloroethane (3 ml) were successively added triethylamine (55 μl) and acetic anhydride (35 μl), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was acidified with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane-methanol (50:50:0-85:0:15) was concentrated under reduced pressure to give the object compound (28.5 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane-methanol (50:50:0-85:0:15)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1be9ad5e88af4269b6a27d531837e08a
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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